Palladium-catalyzed synthesis of carbazoles from N-(2-halophenyl)-2,6-diisopropylanilines via C-C cleavage

Article abstract of DOI:10.1016/j.tetlet.2010.02.098

The synthesis of 1-isopropyl-substituted carbazoles by the palladium-catalyzed dealkylative cyclization of N-(2-halophenyl)-2,6-diisopropylanilines is described. The reaction involves intramolecular C-C bond formation, coupled with the cleavage of a C-X bond and a C-C bond, and is proposed to proceed through the formation of a dearomatized intermediate.